Imidazolidinones

ABSTRACT

1-ARALKYLAMINO- AND 1-ARALKYLIDENEAMINO-2-IMIDAZOLIDINONES, AND DERIVATIVES THEREOF, SUCH AS 1-((3-TRIFLUOROMETHYL)BENZYLIDENEAMINO)-2-IMIDAZOLIDINONE, ARE USED AS HERBICIDES.

United States Patent 3,746,704 IMIDAZOLIDINONES Willy D. Kollmeyer and Kurt H. G. Pilgram, Modesto, Calif., assignors to Shell Oil Company, New York,

No Drawing. Filed May 19, 1971, Ser. No. 145,014

Int. Cl. C07d 49/32 US. Cl. 260-240 F 1 Claim ABSTRACT OF THE DISCLOSURE l-aralkylaminoand 1 aralkylideneamino-Z-imidazolidinones, and derivatives thereof, such as 1-[(3-trifluoromethyl)benzylideneamino]-2-imidazolidinone, are used as herbicides.

FIELD OF THE INVENTION This invention relates to novel compounds and their use for controlling the growth of undesirable plants.

DESCRIPTION OF THE PRIOR ART DESCRIPTION OF THE PREFERRED EMBODIMENT The novel herbicidal compounds of this invention are represented by the generic formula H2C- CH, H-N --R wherein R represents N or N=CHR" \CHT-R R being phenyl or a group represented by R" and R" being phenyl substituted by one or two of chlorine, bromine, fiuorine, alkyl of from 1 to 3 carbon atoms, and/or trifluoromethyl. Also are included the mineral acid salts of these compounds when R is By mineral acids are meant sulfuric acid, phosphoric acid, nitric acid, hydrochloric, hydrobromic, hydrofluoric and hydriodic acids. Preferred are the hydrochloric acid salts.

Preferred compounds are those wherein R is and the HCl salt thereof, or is N=CHR", wherein R" is phenyl substituted by from 1 or 2 chlorine, bromine, methyl, and/or trifluoromethyl groups.

Typical members of this class of herbicides are described and their properties illustrated in the working examples given hereinafter.

Other typical species include:

1- 2- chlorobenzylamino 2-imidazolidinone 1- (2-fluorob enzylamino) -2-imidazolidinone 1- (Z-methylbenzylamino -2-imidazolidinone l- (2-trifiuoromethyl) benzylamino]-2-imidazolidinone 1- 3-trifluoromethyl) -4-chlorobenzylamino] -2- imidazolidinone 1- 3-trifiuoromethyl) -5-chlorobenzylamino] -2- imidazolidinone 1- (3-trifluoromethyl) -6-chlorobenzylamino]-2- imid azolidinone 1- 3-tritiuoromethyl -4-chlorobenzylideneamino] -2- imidazolidinone 1-[ (3-trifluoromethyl) -5-chlorobenzylideneamino] -2- imidazolidinone 1- (3 -trifiuoromethyl -6-chlorobenzylideneamino] -2- imidazolidinone The compounds of the invention are readily prepared by treating 1-amino-2-imidazolidinone with the appropriate aromatic aldehyde in an alcohol solution, followed by hydrogenation if desired. The 1-amino-2-imidazolidinone is prepared according to the method of Michaels and Gever, J. Am. Chem. Soc. 78, 5349 (1956) and the benzaldehyde is prepared by the method of Filler and Novar, J. Org. Chem, 25, 753 (1960). The manner in which the conversion is carried out is illustrated in the examples set out hereinafter.

In these examples, parts means parts by weight unless otherwise expressly indicated, and parts by weight bear the same relationship to parts by volume as does the kilogram to the liter.

In these examples, the structures of the products were established, in each case, by elemental, infra-red spectrum and/ or nuclear magnetic resonance analyses.

EXAMPLE I Preparation of 1-(3-chlorobenzylideneamino)-2- imidazolidinone EXAMPLES II-V Using the method of Example I, the imidazolidinones of Table I were prepared.

TAB LE I Compounds of the formula Meltin Example No. R: point, C

II 2 G-dichlorophenyl 199-201 III 4 chloropheny, 228-229 IV Z-chlorophenyl 206-208 3 EXAMPLE v Preparation of 1- [3- (trifluoromethyl) benzylideneamino]-2-imidazolidinone To a solution of 3.6 parts l-amino-Z-imidazolidinone in 100 par-ts water at 65 C. was added 4.3 parts 3-(tn'- fluoromethyl)benzaldehyde in 50 parts ethanol. The mixture was stirred overnight without further heating. The white crystals were then filtered and combined with additional product obtained by concentrating the filtrate in vacuo. The total solids were thoroughly washed with water and ether and dried. The yield was 60% and the crystals melted at 176-177 C.

EXAMPLES VI-XXI Using the method of Example V the imidazolidinones of Table II were prepared.

TABLE II Compounds of the formula Melting point, 0.

Example No. R2

4 EXAMPLE XXIII Reacting the product of Example with HCl gave the HCl salt, melting point 210-211 C. with decomposition.

EXAMPLE XXIV The pre-emergence herbicidal activity of compounds of the invention was evaluated by planting seeds of test plants in soil treated with the test compounds at the rate of 17.5 pounds per acre. Seeds of watergrass and cress were planted in treated soil and the planted soil held under controlled conditions of temperature, moisture, and light for 13 to 14 days. The amount of germination then was noted, and the elfectiveness of the test compound rated on the basis of a 0 to 9 scale, 0 rating indicating no effect, 9 indicating death of seedlings or no germination. The results are summarized in Table 3. The post-emergence activity of compounds of the invention was evaluated by spraying 10-day old pigweed plants and 7-day old carbgrass plants with a liquid formulation of the test compound at the rate of 10 pounds of test compound per acre. The sprayed plants then were held under controlled conditions of temperature, moisture and light for 10-11 days. The effect of the test chemical then was evaluated visually, the results being rated on a 0 to 9 scale, 0 rating indicating no efiect, 9 rating indicating complete kill of the plants. The results are summarized in Table III. The general phytotoxicity of the compounds was evaluated by planting ryegrass and sowthistle plants in culture solutions treated with the test compounds at 10 parts per million solution. The plants were held under controlled conditions of temperature, moisture, and light for 10 to 11 days. The amount of growth of the roots and shoots was noted, and the effectiveness of the test compound was rated on the basis of a 0 to 9 scale, 0 rating indicating no elfect, 9 indicating death of the plant. The

XXI Hmmo results are also summarized in Table III.

TABLE III Soil Solution Pro-emergence Postremergence Ryegrass Sowthistle Compound of Example Water-grass Cress Orabgrass Pigweed Roots Shoots Roots Shoots m oucomzococcaeowsocowoewcowwmww cocaniqowoo owwwmgnmma oeomgzpa aoqmthoeow mowanomqzetaeowumoq meeocmmo azmwwqwoeccoaawworoee MMQQNNHQQQ'QQKIDMHQQQOMQOU ramuocoocw eaeommqeeqmrauracaoooo romanoo reoowcaomhooooomoeqwmwooe EXAMPLE XX'II Preparation of 1-(benzylamino)-2-imidazolidinone It is evident from the results of these tests that compounds of the invention are potentially valuable herbicides, some having broad-spectrumactivity, whether applied pre-emergence or post-emergence, others being more active applied pre-emergence or post-emergence. Some are effective for controlling nutsedge.

The compounds of this invention are in general solids of very low volatility.

They may be applied as solutions or emulsifiable concentrates in the common organic solvents used in applying herbicides. The compounds of the invention are most readily and effectively applied as herbicides formulated as wettable powders, or as granules for application to soil. Thus, the compound can be adsorbed or absorbed in or on a sorptive carrier, such as finely divided clay, talc, gypsum, lime, Wood flour, fullers earth, kieselguhr, or the like. The solid composition, or dust, may contain from as little as 1% by weight of active material to 75% by weight of active material, or even more. It may be prepared as a dust, or as granules designed to be broadcast or to be worked into the soil. Wettable powders can be prepared suitable for suspension in water with or without the aid of conventional dispersing or deflocculating agents and with or without such adjuvants as oils, stickers, wetting agents, etc.

For field application, the rate of application of the active agent may be varied from about 0.1 to 30 or more pounds per acre. It will be appreciated that the rate of application is subject to variation according to the particular active agent used, the particular species of plants involved, and the local conditions, for example, temperature, humidity, moisture content of the soil, nature of the soil, and the like. Effective resolution of these factors is well within the skill of those well versed in the herbicide art.

The herbicidal compositions may contain one or more of the herbicidal compounds set out hereinbefore as the sole active agent, or they may contain in addition thereto other biologically active substances. Thus, insecticides, e.g., DDT, endrin, dieldrin, aldrin, chlordane, demeton, methoxychlor, DDVP, naled, alpha-methylbenzyl 3-hydroxycrotonate dimethyl phosphate and 3-hydroxy-N,N- dimethyl crotonamide dimethyl phosphate, rotenone and pyrethrum, and fungicides, such as copper compounds, ferbam, captan, and the like, may be incorporated in the compositions. Further, if desired, the herbicidal compositions may contain fertilizers, trace metals, or the like and when applied directly to the soil may additionally contain nematocides, soil conditioners, other plant regulators, such as naphthalene acetic acid, 2,4-dichlorophenoxyacetic acid and the like, and/or additional herbicides of different properties.

I claim as my invention:

1. l [3 (trifluoromethyl)benzylidene-amino] 2- imidazolidinone.

References Cited Jansen et al.: J. Chem. Soc. 1962, pp. 4909 to 4914.

Snyder et a1.: Chemical Abstracts, vol. 73, pp. 3201 (abstract N0. 5602lg), 1970.

Danchev et 211.: Chemical Abstracts, vol. 74, pp. 305-6 (1971), (abstract of Danchev et al., Farmatsiya (Sofia), 1970, No. 20, pp. 1-6).

JOHN D. RANDOLPH, Primary Examiner US. Cl. X.R. 

